Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 68, Issue 6, Pages 2460-2462Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo020658q
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tert-beta-Bromo alcohols, derived from simple monoterpene hydrocarbons, react with zinc sulfide in dimethyl sulfoxide to afford saturated ketones as the major and hydroxy ketones as the minor products. The reaction involves initial nucleophilic attack by DMSO on the carbon attached to the halogen, which is assisted by electrophilic zinc sulfide. Subsequent Kornblum type oxidation yields the alpha-hydroxy ketone. On the other hand, abstraction of proton beta to the hydroxyl group followed by an attack of the neighboring hydroxyl moiety on the sulfur of the dimethylsulfoxonium intermediate and its subsequent collapse yields an enol, which tautomerizes to a saturated ketone. The latter pathway is predominantly followed.
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